10 Signs It’s Time To Update Your Wardrobe

Fall is coming, you ragamuffin. All you need are a few key pieces to go from generic to gent.

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Instead: trade your staid cushioned insoles for a quality pair of brown leather boots or oxfords.

Instead: trade your staid cushioned insoles for a quality pair of brown leather boots or oxfords.

Chukkas, Red Wings, those hiking boots with the metal lace clips — whatever you pick, know that they require even less thought than your go-to sneakers because they go with EVERYTHING.

Clockwise starting from the upper left: Closet Freaks Blog | $162 from ASOS | Red Wings Boots | Closet Freaks Blog | $355 from Russell Moccasin | Best Gear

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